JP3183819B2 - Method for producing 1,1,1,3,3-pentafluoropropane - Google Patents
Method for producing 1,1,1,3,3-pentafluoropropaneInfo
- Publication number
- JP3183819B2 JP3183819B2 JP04764196A JP4764196A JP3183819B2 JP 3183819 B2 JP3183819 B2 JP 3183819B2 JP 04764196 A JP04764196 A JP 04764196A JP 4764196 A JP4764196 A JP 4764196A JP 3183819 B2 JP3183819 B2 JP 3183819B2
- Authority
- JP
- Japan
- Prior art keywords
- pentafluoropropane
- antimony
- reaction
- catalyst
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ポリウレタンフォ−ム
等の発泡剤あるいは冷媒等として有用な１，１，１，
３，３−ペンタフルオロプロパンの製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to 1,1,1,1 useful as a foaming agent such as polyurethane foam or a refrigerant.
The present invention relates to a method for producing 3,3-pentafluoropropane.
【０００２】[0002]
【従来技術】１，１，１，３，３−ペンタフルオロプロ
パンの製造方法としては従来、ＣＦ3−ＣＣｌＸ−Ｃ
Ｆ2Ｃｌを接触水素化する方法（特開平６−２５６２３
５号）、１，１，３，３，３−ペンタフルオロプロペ
ンをＰｄ−Ａｌ2Ｏ3で水素化する方法（Ｉｚｖｅｓｔ．
Ａｋａｄ．Ｎａｕｋ Ｓ．Ｓ．Ｓ．Ｒ．，Ｏｔｄｅｌ．
Ｋｈｉｍ．Ｎａｕｋ．１９６０，１４１２−１８；ＣＡ
５５，３４９ｆ）、１，２，２−トリクロロペンタ
フルオロプロパンを水素化する方法（ＵＳＰ２９４２０
３６号）、１，１，１，３，３−ペンタクロロプロパ
ンを触媒の存在下フッ化水素で液相フッ素化する方法
（ＷＯ９６／０１７９７）などが知られている。2. Description of the Related Art As a method for producing 1,1,1,3,3-pentafluoropropane, conventionally, CF 3 -CClX-C
Method for catalytic hydrogenation of F 2 Cl (JP-A-6-25623)
No. 5), a method of hydrogenating 1,1,3,3,3-pentafluoropropene with Pd-Al 2 O 3 (Izvest.
Akad. Nauk S.D. S. S. R. , Otdel.
Khim. Nauk. 1960, 1412-18; CA
55,349f), a method for hydrogenating 1,2,2-trichloropentafluoropropane (US Pat. No. 2,942,420).
No. 36) and a method of liquid-phase fluorination of 1,1,1,3,3-pentachloropropane with hydrogen fluoride in the presence of a catalyst (WO96 / 01797) and the like are known.
【０００３】[0003]
【発明が解決しようとする課題】前記した特開平６−２
５６２３５号またはＵＳＰ２９４２０３６号などに記載
された水素化による塩素原子の水素置換は反応率および
選択率に優れた方法ではあるが、触媒の劣化が著しく、
また、原料であるフッ素化塩素化物を予め調製しなけれ
ばならず、工業的に適用するには困難な点が多い。一
方、前記で示したオレフィンへの水素付加による方法
はすぐれた１，１，１，３，３−ペンタフルオロプロパ
ンの製造方法であるが、原料となる１，１，３，３，３
−ペンタフルオロプロペンを入手することが困難であり
工業的に採用するには問題がある。SUMMARY OF THE INVENTION The above-mentioned JP-A-6-2
Although hydrogen replacement of chlorine atoms by hydrogenation described in US Pat. No. 56235 or US Pat. No. 2,942,366 is a method excellent in the reaction rate and the selectivity, the deterioration of the catalyst is remarkable.
Further, a fluorinated chlorinated product as a raw material must be prepared in advance, and there are many difficult points for industrial application. On the other hand, the method by hydrogenation to an olefin described above is an excellent method for producing 1,1,1,3,3-pentafluoropropane.
-It is difficult to obtain pentafluoropropene and there is a problem in industrially adopting it.
【０００４】また、ＷＯ９６／０１７９７の方法は、比
較的１，１，１，３，３−ペンタフルオロプロパンの選
択率が低い。In the method of WO96 / 01797, the selectivity of 1,1,1,3,3-pentafluoropropane is relatively low.
【０００５】[0005]
【問題点を解決するための具体的手段】本発明者らはか
かる従来技術の問題点に鑑み、工業的規模での製造に適
した１，１，１，３，３−ペンタフルオロプロパンの製
造方法を確立するべく各種の製造プロセスについて鋭意
検討を加えたところ、対応するフッ素化塩素化物をフッ
化水素で液相フッ素化するにあたって、触媒としてアン
チモン化合物を使用することにより、高収率で目的とす
る１，１，１，３，３−ペンタフルオロプロパンを得る
ことができることを見出し、本発明に到達したものであ
る。SUMMARY OF THE INVENTION In view of the above problems of the prior art, the present inventors have prepared 1,1,1,3,3-pentafluoropropane suitable for production on an industrial scale. After diligent studies on various manufacturing processes to establish a method, the target was obtained in high yield by using an antimony compound as a catalyst in the liquid phase fluorination of the corresponding fluorinated chlorinated product with hydrogen fluoride. The present inventors have found that 1,1,1,3,3-pentafluoropropane can be obtained, and have reached the present invention.
【０００６】すなわち、本発明は、１−クロロ−３，
３，３−トリフルオロプロペンをフッ化水素により液相
フッ素化して１，１，１，３，３−ペンタフルオロプロ
パンを製造する方法であって、触媒としてアンチモン化
合物を使用する方法である。That is, the present invention relates to 1-chloro-3,
This is a method for producing 1,1,1,3,3-pentafluoropropane by subjecting 3,3-trifluoropropene to liquid phase fluorination with hydrogen fluoride, and using an antimony compound as a catalyst.
【０００７】本発明の方法は連続式、バッチ式または半
バッチ式の形式を採用し得るが、以下の詳細な説明では
バッチ式の条件を中心にする。他の形式を採用した場合
に、反応条件を修正することは当業者にとって周知の事
項である。While the method of the present invention may employ a continuous, batch or semi-batch format, the following detailed description focuses on batch conditions. Modifying the reaction conditions when employing other formats is well known to those skilled in the art.
【０００８】本発明に使用する１−クロロ−３，３，３
−トリフルオロプロペンの製造法としては、３，３，３
−トリフルオロプロピンの塩化水素による塩素化反応
（Ｊ．Ｃｈｅｍ．Ｓｏｃ．，１９５２，３４９０．）ま
たは３−クロロ−１，１，１，−トリフルオロ−３−ヨ
ードプロパンのエタノール性ＫＯＨによる脱ヨウ化水素
反応（Ｊ．Ｃｈｅｍ．Ｓｏｃ．，１９５３，１１９
９．）などが知られている。また、本出願人が出願した
特願平８−５９７１には気相中においてフッ素化触媒存
在下、１，１，１，３，３−ペンタクロロプロパンをフ
ッ化水素でフッ素化する方法を開示している。1-chloro-3,3,3 used in the present invention
-The method for producing trifluoropropene includes 3,3,3
-Chlorination reaction of -trifluoropropyne with hydrogen chloride (J. Chem. Soc., 1952, 3490.) or deiodination of 3-chloro-1,1,1, -trifluoro-3-iodopropane with ethanolic KOH Hydrogenation reaction (J. Chem. Soc., 1953, 119)
9. ) Are known. Japanese Patent Application No. 8-5971 filed by the present applicant discloses a method for fluorinating 1,1,1,3,3-pentachloropropane with hydrogen fluoride in the presence of a fluorination catalyst in the gas phase. ing.
【０００９】フッ化水素によるハロゲン化炭化水素の液
相フッ素化におけるアンチモン触媒は、一般にはＳｂＦ
ａＸｂ（Ｘはハロゲン、ａ，ｂはいずれも０〜５であ
り、ａ＋ｂ＝５である。）の混合ハロゲン化状態をとる
ものと推定されているため、本発明においてもアンチモ
ン化合物はその活性状態においては出発化合物に拘わら
ずこの様な混合ハロゲン状態を採るものと考えられる。
また、ハロゲン化アンチモンは塩素、臭素、沃素、フッ
素により容易にその非活性状態である３価から活性状態
である５価に酸化されるので必ずしも反応系に導入する
ときから５価のアンチモンを使用する必要はない。The antimony catalyst in the liquid phase fluorination of halogenated hydrocarbons with hydrogen fluoride is generally SbF
aXb (X is a halogen, a and b are each 0 to 5 and a + b = 5) is assumed to be in a mixed halogenated state, and therefore, in the present invention, the antimony compound is in its active state. Is considered to adopt such a mixed halogen state regardless of the starting compound.
In addition, since antimony halide is easily oxidized from trivalent (inactive state) to pentavalent (active state) by chlorine, bromine, iodine and fluorine, pentavalent antimony is always used from the time of introduction into the reaction system. do not have to.
【００１０】したがって、本発明でアンチモン触媒を用
いる場合、３価もしくは５価のハロゲン化アンチモンま
たはアンチモン金属を出発原料とすれば目的を達するこ
とができる。そこで、アンチモン化合物を具体的に挙げ
ると、五塩化アンチモン、五臭化アンチモン、五沃化ア
ンチモン、五フッ化アンチモン、三塩化アンチモン、三
臭化アンチモン、三沃化アンチモン、三フッ化アンチモ
ンを例示できるが、五塩化アンチモンまたは三塩化アン
チモンが最も好ましい。Therefore, when an antimony catalyst is used in the present invention, the object can be achieved by using trivalent or pentavalent antimony halide or antimony metal as a starting material. Thus, specific examples of antimony compounds include antimony pentachloride, antimony pentabromide, antimony pentaiodide, antimony pentafluoride, antimony trichloride, antimony tribromide, antimony triiodide, and antimony trifluoride. Although possible, antimony pentachloride or antimony trichloride is most preferred.
【００１１】本発明の方法において、触媒濃度は１−ク
ロロ−３，３，３−トリフルオロプロペンに対して０．
１〜５０モル％が好ましく、１０〜３０モル％がより好
ましい。０．１モル％以下では１−クロロ−３，３，３
−トリフルオロプロペンの反応率、１，１，１，３，３
−ペンタフルオロプロパンの収率が共に低下し、また５
０モル％以上では高沸点化合物からなるタ−ルの生成量
が増加し、触媒劣化が著しいので好ましくない。In the method of the present invention, the catalyst concentration is 0.1 to 1-chloro-3,3,3-trifluoropropene.
1 to 50 mol% is preferable, and 10 to 30 mol% is more preferable. At 0.1 mol% or less, 1-chloro-3,3,3
-Conversion of trifluoropropene, 1,1,1,3,3
-The yield of pentafluoropropane both decreased and
If it is 0 mol% or more, the amount of tar formed of a high-boiling compound increases, and the catalyst deteriorates remarkably.
【００１２】反応温度は１０〜１５０℃が好ましく、５
０〜１３０℃がより好ましい。１０℃以下では１−クロ
ロ−３，３，３−トリフルオロプロペンの反応率、１，
１，１，３，３−ペンタフルオロプロパンの収率共低下
し、また１５０℃以上ではタ−ル生成量が増加し、触媒
劣化が著しい。The reaction temperature is preferably from 10 to 150 ° C.
0-130 degreeC is more preferable. At 10 ° C. or lower, the conversion of 1-chloro-3,3,3-trifluoropropene is 1,
The yield of 1,1,3,3-pentafluoropropane decreases together. At 150 ° C. or higher, the amount of tar increases and the catalyst deteriorates remarkably.
【００１３】１−クロロ−３，３，３−トリフルオロプ
ロペンに対するフッ化水素のモル比は２〜３０の範囲が
好ましく、特に好ましくは３〜２０である。２モル倍未
満では１−クロロ−３，３，３−トリフルオロプロペン
の反応率は十分高くなく、３０モル倍を超えても１−ク
ロロ−３，３，３−トリフルオロプロペン反応率の向上
は認められず、未反応フッ化水素回収の点からも経済的
に有利でない。The molar ratio of hydrogen fluoride to 1-chloro-3,3,3-trifluoropropene is preferably in the range of 2 to 30, and particularly preferably 3 to 20. If it is less than 2 moles, the conversion of 1-chloro-3,3,3-trifluoropropene is not sufficiently high, and if it exceeds 30 moles, the conversion of 1-chloro-3,3,3-trifluoropropene is improved. Is not recognized, and it is not economically advantageous from the viewpoint of recovering unreacted hydrogen fluoride.
【００１４】反応に必要な圧力は反応温度にもよるが、
反応器内で反応混合物を液相の状態に保てれば良く、
１．０〜１００Ｋｇ／ｃｍ2が好ましく、５〜３０Ｋｇ
／ｃｍ2がより好ましい。The pressure required for the reaction depends on the reaction temperature.
What is necessary is just to keep the reaction mixture in a liquid phase in the reactor,
1.0-100 kg / cm 2 is preferred, and 5-30 kg
/ Cm 2 is more preferred.
【００１５】本発明においては、反応の調節、触媒劣化
の防止を目的として反応系に溶媒を共存させることがで
きる。溶媒としては、目的物である１，１，１，３，３
−ペンタフルオロプロパンを使用してもよいし、または
テトラクロロエタン等の塩素化を受けにくい多塩素化物
を使用することが好ましい。In the present invention, a solvent can coexist in the reaction system for the purpose of controlling the reaction and preventing catalyst deterioration. As the solvent, 1,1,1,3,3
-Pentafluoropropane may be used, or it is preferable to use a polychlorinated compound which is not easily subjected to chlorination such as tetrachloroethane.
【００１６】本発明の触媒は、劣化した場合あるいは触
媒原料として五価以外の化合物を使用した場合には、容
易に五価の活性化状態に活性化することができる。この
方法は、１−クロロ−３，３，３−トリフルオロプロペ
ン、１，１，１，３，３−ペンタフルオロプロパンある
いは上記したいずれかの溶媒の存在下、１０℃〜１００
℃で塩素を導入することよりなっている。必要に応じて
攪拌を行なうことも可能である。塩素の量は、触媒のモ
ル数の１〜１００倍のモル数を用いる。１０℃以下では
活性化するのに長時間を要し、１００℃以上では共存す
る１−クロロ−３，３，３−トリフルオロプロペン、
１，１，１，３，３−ペンタフルオロプロパンあるいは
上記した溶媒の塩素化がおこり好ましくない。The catalyst of the present invention can be easily activated to a pentavalent activated state when it has deteriorated or when a compound other than pentavalent is used as a catalyst raw material. This method is carried out in the presence of 1-chloro-3,3,3-trifluoropropene, 1,1,1,3,3-pentafluoropropane or any of the above-mentioned solvents at a temperature of 10 ° C to 100 ° C.
Introducing chlorine at ° C. Stirring can be performed if necessary. The amount of chlorine used is 1 to 100 times the number of moles of the catalyst. It takes a long time to activate at 10 ° C or lower, and coexists with 1-chloro-3,3,3-trifluoropropene at 100 ° C or higher,
Chlorination of 1,1,1,3,3-pentafluoropropane or the above-mentioned solvent occurs, which is not preferable.
【００１７】本発明の方法は、バッチ式、生成物のみを
反応器から除去しながら行う半バッチ式または流通式反
応装置において実施することができるが、それぞれの反
応装置において、当業者が容易に調節しうる程度の反応
条件の変更を妨げるものではない。The process of the present invention can be carried out in a batch mode, a semi-batch mode or a flow mode reactor in which only the product is removed from the reactor. It does not prevent the reaction conditions from being changed to an adjustable degree.
【００１８】本発明の反応を行う反応器は、ハステロ
イ、ステンレス鋼、モネル、ニッケルなど、あるいはこ
れらの金属または四フッ化エチレン樹脂、クロロトリフ
ルオロエチレン樹脂、フッ化ビニリデン樹脂、ＰＦＡ樹
脂などを内部にライニングした材質で製作したものが好
ましい。The reactor for carrying out the reaction of the present invention contains Hastelloy, stainless steel, Monel, nickel or the like, or a metal such as these, or tetrafluoroethylene resin, chlorotrifluoroethylene resin, vinylidene fluoride resin, PFA resin or the like. It is preferable to use a member made of a material lined with the above.
【００１９】本発明の方法で製造された１，１，１，
３，３−ペンタフルオロプロパンは、フッ素化反応生成
物について公知の方法を適用して精製されるが、例え
ば、塩化水素、未反応のフッ化水素とともに反応器から
液体または気体状態で取り出された後、過剰のフッ化水
素が液相分離などの操作で除去され、ついで、水または
塩基性水溶液で酸性成分を除いた後、蒸留により目的と
する高純度の１，１，１，３，３−ペンタフルオロプロ
パンとされる。The 1,1,1, produced by the method of the present invention
The 3,3-pentafluoropropane is purified by applying a known method to the fluorination reaction product, for example, withdrawn from the reactor in a liquid or gas state together with hydrogen chloride and unreacted hydrogen fluoride. Thereafter, excess hydrogen fluoride is removed by an operation such as liquid phase separation, and then acidic components are removed with water or a basic aqueous solution, and then the desired high-purity 1,1,1,3,3 is obtained by distillation. Pentafluoropropane.
【００２０】[0020]
【実施例】以下、実施例により本発明を詳細に説明す
る。 実施例１ 還流冷却器と攪拌機を備えたＳＵＳ３１７製１ｌオ−ト
クレ−ブに触媒として五塩化アンチモン０．０５３モル
（１５．９ｇ）、フッ化水素５．０モル（１００ｇ）及
び、１−クロロ−３，３，３−トリフルオロプロペン
０．２６５モル（３４．６ｇ）を仕込み、攪拌しながら
反応温度を７１℃に昇温し、反応中７１〜７４℃に保っ
た。反応の進行と共に発生する塩化水素により圧力は上
昇するが、１０Kg/cm2になった時点で還流冷却器を通し
て塩化水素の抜出しを開始し、その後反応圧力を１０Kg
/cm2に保った。The present invention will be described below in detail with reference to examples. Example 1 In a 1 liter autoclave made of SUS317 equipped with a reflux condenser and a stirrer, 0.053 mol (15.9 g) of antimony pentachloride, 5.0 mol (100 g) of hydrogen fluoride and 1-chlorohydrogen were used as catalysts. -3,3,3-trifluoropropene
0.265 mol (34.6 g) was charged and the reaction temperature was raised to 71 ° C. while stirring, and kept at 71 to 74 ° C. during the reaction. The pressure rises due to hydrogen chloride generated as the reaction proceeds, but when the pressure reaches 10 kg / cm 2 , extraction of hydrogen chloride is started through a reflux condenser, and then the reaction pressure is increased to 10 kg / cm 2.
/ cm 2 .
【００２１】反応開始３時間後、反応器を室温まで冷却
し、圧力を常圧まで下げることにより反応器から流出し
たガスを水層を通した上で、ドライアイス−メタノール
で冷却されたトラップに捕集した。この捕集物とオ−ト
クレ−ブの内容物を塩酸で洗浄し、さらに水で洗浄して
得られた２８．７ｇの有機物をガスクロマトグラフによ
り分析し、反応生成物組成を求めた。結果を表１に示
す。After 3 hours from the start of the reaction, the reactor was cooled to room temperature, and the pressure was reduced to normal pressure. The gas flowing out of the reactor was passed through an aqueous layer, and was then placed in a trap cooled with dry ice-methanol. Collected. The collected substance and the contents of the autoclave were washed with hydrochloric acid and further washed with water, and 28.7 g of an organic substance obtained was analyzed by gas chromatography to determine the composition of the reaction product. Table 1 shows the results.
【００２２】[0022]
【表１】 [Table 1]
【００２３】実施例２ 還流冷却器と攪拌機を備えたＳＵＳ３１７製１ｌオ−ト
クレ−ブに触媒として五塩化アンチモン０．１モル（２
９．９ｇ）、フッ化水素５．０モル（１００ｇ）、１，
１，２，２−テトラクロロエタン０．３モル（５０．４
ｇ）及び、１−クロロ−３，３，３−トリフルオロプロ
ペン １．０モル（１３０．５ｇ）を仕込み、攪拌しな
がら反応温度を６５℃に昇温し、反応中６５〜７０℃に
保った。反応の進行と共に発生する塩化水素により圧力
は上昇するが、８．５Kg/cm2になった時点で還流冷却器
を通して塩化水素の抜出しを開始し、その後反応圧力を
８．５Kg/cm2に保った。Example 2 A 1 liter autoclave made of SUS317 equipped with a reflux condenser and a stirrer was used as a catalyst to prepare 0.1 mol of antimony pentachloride (2 moles).
9.9 g), 5.0 mol (100 g) of hydrogen fluoride, 1,
0.3 mol of 1,2,2-tetrachloroethane (50.4
g) and 1.0 mol (130.5 g) of 1-chloro-3,3,3-trifluoropropene were added, and the reaction temperature was raised to 65 ° C. while stirring, and maintained at 65 to 70 ° C. during the reaction. Was. The pressure increases due to hydrogen chloride generated as the reaction proceeds, but when the pressure reaches 8.5 kg / cm 2 , extraction of hydrogen chloride is started through a reflux condenser, and thereafter, the reaction pressure is maintained at 8.5 kg / cm 2 . Was.
【００２４】反応開始３時間後、反応器を室温まで冷却
し、圧力を常圧まで下げることにより反応器から流出し
たガスを水層を通した上で、ドライアイス−メタノール
で冷却されたトラップに捕集した。この捕集物とオ−ト
クレ−ブの内容物を塩酸で洗浄し、さらに水で洗浄して
得られた１４９ｇの有機物をガスクロマトグラフにより
分析し、反応生成物組成を求めた。３５％の溶媒が含ま
れていたが、溶媒を除いた結果を表１に示す。After 3 hours from the start of the reaction, the reactor was cooled to room temperature, the pressure was reduced to normal pressure, and the gas flowing out of the reactor was passed through an aqueous layer, and then placed in a trap cooled with dry ice-methanol. Collected. The collected substance and the contents of the autoclave were washed with hydrochloric acid and further washed with water, and 149 g of an organic substance obtained was analyzed by gas chromatography to determine a reaction product composition. Table 1 shows the results when 35% of the solvent was contained but the solvent was removed.
【００２５】[0025]
【発明の効果】本発明の方法は、高収率で１，１，１，
３，３−ペンタフルオロプロパンを製造することができ
るという効果を有する。The method of the present invention provides 1,1,1,1 with a high yield.
There is an effect that 3,3-pentafluoropropane can be produced.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 日比野 泰雄 埼玉県川越市今福中台2805番地 セント ラル硝子株式会社東京研究所内 (56)参考文献 特開 平９−183740（ＪＰ，Ａ) 特開 平９−110737（ＪＰ，Ａ) 特開 平８−239334（ＪＰ，Ａ) 特開 平８−104655（ＪＰ，Ａ) 特開 平５−201892（ＪＰ，Ａ) 特表 平９−508138（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 19/08 C07C 17/21 C07B 61/00 ────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yasuo Hibino 2805 Imafukunakadai, Kawagoe-shi, Saitama Tokyo Central Research Laboratory (56) References JP-A-9-183740 (JP, A) JP-A Heihei 9-110737 (JP, A) JP-A-8-239334 (JP, A) JP-A-8-104655 (JP, A) JP-A-5-201892 (JP, A) Table 9-508138 (JP, A) A) (58) Field surveyed (Int. Cl. 7 , DB name) C07C 19/08 C07C 17/21 C07B 61/00
Claims (3)
ロペンをアンチモン触媒存在下フッ化水素により液相フ
ッ素化することを特徴とする１，１，１，３，３−ペン
タフルオロプロパンの製造方法。1. A liquid phase fluorination of 1-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of an antimony catalyst, and characterized in that 1,1,1,3,3-pentafluoropropane is provided. Manufacturing method.
（ハロゲンは、塩素、臭素、沃素、フッ素をいう。）で
ある請求項１記載の１，１，１，３，３−ペンタフルオ
ロプロパンの製造方法。2. The process for producing 1,1,1,3,3-pentafluoropropane according to claim 1, wherein the antimony catalyst is antimony pentahalide (halogen means chlorine, bromine, iodine or fluorine). .
１．０〜１００．０ｋｇ／ｃｍ2とすることを特徴とす
る請求項１〜２記載の１，１，１，３，３−ペンタフル
オロプロパンの製造方法。3. The method according to claim 1, wherein the reaction temperature is 10 to 150 ° C. and the reaction pressure is 1.0 to 100.0 kg / cm 2. A method for producing pentafluoropropane.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04764196A JP3183819B2 (en) | 1996-03-05 | 1996-03-05 | Method for producing 1,1,1,3,3-pentafluoropropane |
| US08/982,803 US6316681B1 (en) | 1996-03-05 | 1996-12-04 | Method for producing 1,1,1,3,3-pentafluoropropane |
| US09/166,838 US6198010B1 (en) | 1996-03-05 | 1998-10-06 | Method for producing 1,1,1,3,3-pentafluoropropane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04764196A JP3183819B2 (en) | 1996-03-05 | 1996-03-05 | Method for producing 1,1,1,3,3-pentafluoropropane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09241188A JPH09241188A (en) | 1997-09-16 |
| JP3183819B2 true JP3183819B2 (en) | 2001-07-09 |
Family
ID=12780876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04764196A Expired - Fee Related JP3183819B2 (en) | 1996-03-05 | 1996-03-05 | Method for producing 1,1,1,3,3-pentafluoropropane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3183819B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6001218B1 (en) * | 2015-01-30 | 2016-10-05 | オリンパス株式会社 | Endoscope and rigid member |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10309464A (en) * | 1997-03-12 | 1998-11-24 | Daikin Ind Ltd | Manufacture of 1,1,1,3,3-pentafluoropropane |
| BE1011765A3 (en) * | 1998-02-26 | 2000-01-11 | Solvay | HYDROCARBONS hydrofluorination process. |
| JP4389389B2 (en) | 1998-11-13 | 2009-12-24 | ダイキン工業株式会社 | Azeotropic composition comprising 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene, separation and purification method using the same, and 1,1,1 Of 3,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene |
-
1996
- 1996-03-05 JP JP04764196A patent/JP3183819B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6001218B1 (en) * | 2015-01-30 | 2016-10-05 | オリンパス株式会社 | Endoscope and rigid member |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09241188A (en) | 1997-09-16 |
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